David Berman (center), hanging with the kids: Guitarist William Tyler and wife and bassist Cassie Berman

In 1996, Natural Bridge, the second album from Silver Jews, soundtracked my first semester at college. My assigned roommate never showed up, and in the dark of my very own private dorm room, I would envision myself as the "sad king trapped in his golden room," that frontman David Berman sang of in "Black and Brown Blues." As an aspiring artist, the album showed me that music could be forthcoming even in the midst of taking the piss.

Two years later, Berman's third album, American Water, became my fall jogging score after I transferred to University of Virginia, his own alma mater. American Water may well be the Jews' crowning achievement, with Berman's sometime collaborator, Pavement guitarist Stephen Malkmus, injecting the songs with new musicality. Malkmus' angular chops and charismatic singing created the perfect showcase for Berman at the top of his lyrical game. Going past the bad parts of town, for instance, this line from "Smith and Jones Forever"—"When the sun sets on the ghetto/ all the broken stuff gets cold"—always came in at just the right spot. During the rabble-rousing climax "We Are Real," he concluded, "We've been raised on replicas/ of fake and winding roads/ and day after day upon this beautiful stage/ we've been playing tambourine for minimum wage/ but we are real."

As a kid growing up away at college, the road imagery was perfect for setting off down Jefferson Park Avenue in Charlottesville, passing by all the places that had grown familiar.

Throughout his 16-year recording career, Berman has crafted elliptical lines that elevate style over substance, yet simultaneously deliver thoughtful commentary. Berman's knack for skillfully juxtaposing the more mundane elements of modern American existence with surreal, often blackly humorous insight sets him apart from other songwriters. He has a voice (somehow audible even if you read his lyrics alone on paper) that's instantly recognizable, like an old friend you can always rely on for advice. It just happens that the old friend can sum up everything you've ever thought about urban decay with a single couplet.

That manner of mixing loosely associated lyrics with flashes of brilliant observations was smart without being overly serious. The mix seemed tailor-made for me, the 20-year-old coping with new responsibilities that he wasn't quite ready to accept. That was the essence of Berman's style, and it spoke to me.

This past June, Berman released his sixth album as Silver Jews, Lookout Mountain, Lookout Sea, and it represents the biggest artistic shift of his career. With the exception of a few Dylanesque narratives, Berman's characteristic quirky lyrical flourishes are largely absent. Upon first listen, some of the songs sound as if they could have been written by any ol' Nashville songwriter. It's surreal—but not in the usual Silver Jews way—to encounter these wholly irony-free lyrics from Berman: "We could be looking for the same thing/ if you're looking for someone/ We could belong to each other/ if you're not seeing anyone." One could picture Kenny Rogers and Dolly Parton singing this song in 1983.

But that's not a slight, exactly. If you give Lookout Mountain some repeated listens, or read what Berman's said about the record, it's clear that his goals have simply changed: Berman, 41, has said he is speaking to a younger generation for the first time now. He wants his music to offer a pedagogical aspect to its listeners that it previously didn't possess. When a writer is not necessarily trying to communicate a particular message, the lyrics can bounce around freely from one theme to the next. On those early records, there are no constraints. It becomes a much more nuanced enterprise when one wants to communicate some real kernel of truth and provide a continuity of vision throughout the entire work. On a Lookout tune like "What is Not but Could Be If," devices like irony and sly cultural references would only get in the way of serving the song's message of perseverance. If the meaning behind a song is the guiding element, then Berman has to rein in his old verbal theatrics to avoid undermining it. Content, then, has overtaken style.

It's certainly inspiring to hear anyone with the confidence to impart some wisdom to the children of the '80s and '90s, especially in the midst of a recession, a seemingly endless war, and uncertainty in every direction. And this new artistic approach suits the man—who's been through a lot in his 41 years—quite well. But, as a fan of the Jews since 1994, as a writer of songs that have been immensely impacted by old D.C.B., I have to say that regardless of his intentions, Berman's entire catalog has been and continues to be instructive. And not just for aspiring writers or bands, or music nerds with eccentric tastes, but for anyone who is simply drawn to the kind of song that rewards close readings.

Of course, I could be wrong about that last bit: I've long loved how Berman's style seemed to alienate most people. I brought "The Frontier Index," the ninth song on Natural Bridge, into a freshman poetry class back in 1996. Almost no one knew what to make of it. One verse, lifted apparently from a joke that country singer Randy Travis told at a concert, goes: "Boy wants a car from his dad/ Dad says, 'First you gotta cut that hair'/ Boy says, 'Hey Dad, Jesus had long hair'/ and Dad says, 'That's right, son: Jesus walked everywhere.'" Berman took a bit of down-home wisdom and stuck it in the alien context of an indie rock song. It was as brilliant to me as it was incomprehensible to my fellow classmates, who thought the song was about a father/son conflict. I still laugh at that interpretation.

So, like Pavement, the Jews provided another way to feel superior to the herd. I'm really not proud of that. But then, back when I was 18, we were all probably looking for the same thing, anyway.